


Never Really Over

by AmeliaSPN1973



Category: Supernatural
Genre: Age Difference, Car Sex, F/M, Love, Not Beta Read, Pining, Romance, Sex, Smut, losing virginity
Language: English
Status: Completed
Published: 2019-06-21
Updated: 2019-06-20
Packaged: 2020-05-15 17:23:36
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,619
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19300327
Author URL: https://archiveofourown.org/users/AmeliaSPN1973/pseuds/AmeliaSPN1973
Summary: You and Dean keep falling in and out with each other over a twenty year span.





	1. Chapter 1

**Author's Note:**

> Loosely inspired by the song Never Really Over by Katy Perry  
> I'm losing my self-control  
> Yeah, you're starting to trickle back in  
> But I don't wanna fall down the rabbit hole  
> Cross my heart, I won't do it again  
> I tell myself, tell myself, tell myself, "Draw the line"  
> And I do, I do  
> But once in a while, I trip up, and I cross the line  
> And I think of you  
> Two years, and just like that  
> My head still takes me back  
> Thought it was done  
> But I guess it's never really over  
> Oh, we were such a mess  
> But wasn't it the best?  
> Thought it was done  
> But I guess it's never really over  
> Just because it's over doesn't mean it's really over  
> And if I think it over, maybe you'll be comin' over again  
> And I'll have to get over you all over again  
> Just because it's over doesn't mean it's really over  
> And if I think it over, maybe you'll be comin' over again  
> And I'll have to get over you all over again  
> I guess I could try hypnotherapy  
> I gotta rewire this brain  
> 'Cause I can't even go on the internet  
> Without even checking your name  
> I tell myself, tell myself, tell myself, "Draw the line"  
> And I do, I do  
> But once in a while, I trip up, and I cross the line  
> I think of you  
> Two years, and just like that  
> My head still takes me back  
> Thought it was done  
> But I guess it's never really over  
> Oh, we were such a mess  
> But wasn't it the best?  
> Thought it was done  
> But I guess it's never really over  
> Just because it's over doesn't mean it's really over  
> And if I think it over, maybe you'll be comin' over again  
> And I'll have to get over you all over again  
> Just because it's over doesn't mean it's really over  
> And if I think it over, maybe you'll be comin' over again  
> And I'll have to get over you all over again  
> Thought we kissed goodbye  
> Thought we meant this time was the last  
> But I guess it's never really over  
> Thought we drew the line  
> Right through you and I  
> Can't keep going back  
> I guess it's never really over, hey  
> Two years, and just like that  
> My head still takes me back  
> Thought it was done  
> But I guess it's never really over  
> Just because it's over doesn't mean it's really over  
> And if I think it over, maybe you'll be comin' over again  
> And I'll have to get over you all over again  
> And I'll have to get over you all over again  
> Just because it's over doesn't mean it's really over  
> And if I think it over, maybe you'll be comin' over again  
> And I'll have to get over you all over again  
> Over you all over again  
> Thought we kissed goodbye  
> Thought we meant this time was the last  
> But I guess it's never really over  
> Thought we drew the line  
> Right through you and I  
> Can't keep going back  
> I guess it's never really over

You met the Winchester brothers years ago as children when they hunted with their dad and you hunted with yours. Your dad was going out for revenge for the demon who killed your mother and so was John. You spent many days and nights in hotels with those boys. While Sam and you were like brother and sister, you and Dean had a connection that went beyond familial, even though you were six years his senior; it was a romantic connection, even though neither of you knew what love was at the time. Even though your father got adjoining rooms while he and John went on their hunts, Dean would come into your room, leaving the adjoining room door open to listen for Sam, and curl up in your bed with you. You didn’t initiate it, but you allowed him to because of your connection with him. Many nights his arms would wrap around you; his head was buried in your chest. 

You both made it through your awkward years still caring for each other. You continued hunting with your father, not having much time to date or meet guys your age, unless you met them at school or your daddy approved, while Dean got to experience life and lust with women he chose while his father hunted. However, deep down, Dean still wanted you and you wanted him despite how wrong you felt for it.

——————————————

It was age 24 that you remembered most because 1) he confessed his feelings for you, and you confessed your feelings for him and 2) you lost your virginity to Dean, age 18, in the back of a brokedown van parked in the sea of junk cars of Bobby Singer’s place while his dad, your dad, and Bobby played cards inside.

Earlier that day, you and Dean were hanging out in the van, making out and listening to classic rock. When his hand reached down your pants and he began to rub your clit, you pulled back. “Dean. We can’t.”

“Why not sweetheart?”

You were embarrassed. How do you tell the guy you like but is 6 years younger that you never had full sexual intercourse, not because you couldn’t or didn’t have the opportunity, but deep down you didn’t want to because you wanted Dean. “I’m too old for you, Dean. This isn’t right.” 

He smiled. “I like my women older, Y/N. I’m 18 now, and I have liked you for as long as I can remember. I’m no virgin, that is for sure, but I would love to be with you.” His olive green eyes pierced yours and your heart skipped a beat. Your heart always skipped beats around him. He was beautiful and he cared for you. You stared at Dean and his confession he just made to you. You felt it was time to confess to him. “Well, I am.”

“You are what sweetheart?” He looked at you confused. 

“A Virgin.” You looked down, embarrassed.

He put his finger under your chin and raised you to his face. “Look at me Y/N.”

You opened your eyes.

“You don’t how much I would like to be your first.”

“Really?” You smiled. You secretly wanted Dean for so long as well, and to have your first time being with him would be amazing. 

“Please say yes sweetheart.” He wasn’t pleading, but he wanted you to know how much he wanted you.

You thought about it and looked into his olive green eyes.  _ It’s now or never.  _ “OK.”

He smiled and kissed you, leaning you back on the seat, slipping his hand further down your panties near your entrance, but you pulled his hand away. “But not right now.”

“Why?” He was battling an erection and you confused him again. 

“Dean, I want it to be romantic. I’m not talking about hotels, flowers,  and candles. I just don’t want it to be rushed and this could be rushed. I just want us to take it slow, feel everything, and enjoy ourselves.”

He smiled. “OK. Maybe tonight? Midnight. We can sneak out of our rooms and meet here. We’d have all night Baby.”

You smiled. “OK.”

You continued to make out with him, letting him knead your breasts. His tongue moved in your mouth and his body was flushed with yours as you felt his hardness against your stomach. You finally pulled away when you heard John and your dad call out your names for dinner. 

“We gotta go.” You started to get up. 

“Give me just a minute.” His lips nipped your earlobe.

“I don’t want my dad to be on alert, so I need to go now. 

“OK sweetheart. I’ll be right in. I have to calm down. You have me so fucking hard right now.” He grabbed your hand bringing it to the bulge in his jeans. You gently began to palm him and he grunted. “Oh Fuck. You’re gonna make me come.”

“I’m sorry Dean.”

“Don’t be sorry sweetheart. I need to deal with this. I’ll see you later,” he said as he pecked your lips.

You got out of the van and headed towards Bobby’s while he stayed in the van, taking care of his business.

You were physically nervous at dinner for the night ahead. 

Your dad looked at you. “You OK pumpkin?”

“Yeah Dad. It’s just warm outside and I am tired.”

“OK. I just don’t want you to coming down with something. We can leave if you think you’re getting sick.”

“No Dad.” 

Dean almost choked as you responded to your dad. 

“I’m OK. I like it here.” You smiled.

“You OK Dean,” John asked.

“Yes Sir. Fine.”

“OK Y/N.” Your father responded to you. 

After dinner you excused yourself and went to the bathroom and took a long hot bath, shaving everything and then in just your towel,

You went back to your room and laid down, trying to relax the butterflies in your stomach. 


	2. Chapter 2

It was a hot, steamy night as you and Dean snuck out of your rooms and met up outside while Sam, your fathers, and Bobby slept. Dean was a gentleman, despite his bravado. He grabbed your hand and gently pulled you towards the junkyard. “Just follow me sweetheart.”

When he opened the doors to the van, you gasped. He had the backseat made with clean sheets, a blanket, emergency lights for ambiance, the windows down but curtained, and a small boom box that was playing the classic rock station.

You smiled and looked at him and he smiled back. “I wanted tonight to be perfect for you Y/N.”

Dean was no virgin, but he wanted to please you. 

“Wow Dean. This is perfect in your way.”

He placed his palms to your face and kissed you passionately, setting a fire in your belly as you reached your arms around his neck and began to card his hair. 

He lifted you up into the van and then got in, closing the door behind him. You both sat down on the makeshift bed when he leaned in and kissed you, leaning you back. You kissed for awhile, making out, kissing each other’s necks, and feeling each other from the outside of your clothes. 

When he slipped his hand down your sleep shorts, cupping your mound and began to rub your clit, your body erupted in heat for him. Grabbing his shirt end, you peeled it off of him. Taking the hint, he pulled your shirt off, reached up, and kneaded your breasts through your bra. You raised yourself so he could unclasp your bra and pull the straps down and off. 

He kissed down from your neck along your collarbone down until he puckered his lips around your nipple, making it hard. “Oh God Dean.”

“Your breasts are amazing Y/N! I love how you respond to me.”

You began to feel his bulge against your stomach as he began to slip his knee between your legs. Immediately you began to grind against him,  pressure building. You reached up and palmed his bulge through his pants. “Sonofabitch. You can’t do that babe. I won’t last if you get me any harder.”

You stopped and pulled back. “I’m sorry.”

“Y/N. Don’t be.”

He leaned back in kissing in between your breasts then kissing down your torso until he reached the waistband of your shorts. Looking up at you for permission, you smiled and he pulled them down slowly only to see you were not wearing any panties. “Oh sweetheart. I can’t believe you went commando.”

“I didn’t think about this. I just wore what I always wear to sleep.”

Dean bit his lip. “Fuck Y/N. You can’t tell me that because all I’m going to do now is remember your beautiful pussy under those shorts when I think of you asleep or see you in those sleep shorts.”

You laughed as he moved back up to kiss you and you began to pull down the sweatpants he sleeps in. He was commando too. “I guess I’m not the only one that sleeps commando under my pants. I will now think of your hardness underneath those sweats.

You both laughed moment.

Once you were both naked you looked down at his manhood. 

“Like what you see sweetheart?” He smiled.

“It’s not like I haven’t seen a penis before Dean. Just because I have never done it doesn’t mean I haven’t been close, gave a blow job or had an orgasm before.”

“Oh.” Dean looked at you almost disappointed. 

“But man! You are Wow! Yeah. I’ve gotten close a few times, but they didn’t mean anything to me and I couldn’t let it go further, because deep down, I always wanted you to be my first.” You had waited a long time for Dean to be old enough in your eyes to be with him. You had both cared about each other for years, but the six year age difference kept you both from giving in to his advances sooner. When he turned 18, you decided he was an adult and it was his decision, so when you were talking earlier in the day and you confessed your virginity and Dean offered up his ‘services’ immediately, you knew you wanted to. 

He smiled as he leaned in, kissing along your torso, down over your pubic bone down to your inner thigh. 

He peppered tender, wet kisses along your inner thighs which caused you to moan. The feelings he was giving you were beyond incredible. However, that didn’t compare to the moment he licked up your slit, pulled in your clit, and sucked. 

“Holy Fuck!” Your back arched, your toes curled and you reached down running your hands through his hair encouraging him further. He continued as he sucked harder and slipped a finger into your entrance. “Holy Fuck Dean!”  One finger became two as he began to scissor your entrance, opening you up for him. “Damn Baby. You are so wet for me.”

Finally you felt your walls clench around his fingers and your vision go white as you came on him. He continued sucking on the nub, working you through your orgasm, but you were embarrassed for coming all over his face. “Oh God Dean, I’m so sorry.” 

Dean kissed up your body as he moved up to your face. “Don’t be sorry. That was beautiful.” He kissed you as you tasted yourself on his tongue. 

“You were amazing.” You smiled.

He smiled. “I aim to please.”

You began making out with him again, as Dean moved between your legs, and you began to grind against him again for friction. He pulled away, his olive green eyes pierced yours. “You OK to continue?”

“Oh God Yes! Yes Dean. Please. I want you in me.”

He raised himself as you watched him open a condom wrapper and slowly rolled it up his length. You looked his erection and wondered how that was going to fit in you, but you were also intrigued. He was beautiful.

He interlocked his hand with yours and pushed himself in you. Feeling a stretch, you moaned; his girth feeling like he was tearing you, yet you wanted more. 

“You OK?” He could see you wince. 

You looked up and smiled. “Yes Dean.”

“Oh God. You feel so good Y/N. So warm. So wet. You just have to tell me if anything gets too much, OK?”

“OK.”

He pulled back, almost out, and pushed back in causing you to moan loudly. You dug into his biceps as you felt him stretch you further, yet you wanted him too. “Oh God Yes!”

“Fuck Y/N.” He grunted. He continued thrusting as you wrapped your legs around his waist changing the angle and your arms running up and down his back; he was now hitting your g-spot. You could feel the van begin to sway with your thrusts; the old shocks on the van squeaking with each thrust, but you didn’t care. You were caught up in the ecstasy that Dean was giving you. 

“Oh Fuck. Yes! Oh Shit Dean!”

He continued, grunting as you began to buck against him. His pace was becoming brutally erratic as you felt your slapping skins, and you knew he was probably going to falter soon. 

“Come on sweetheart. I need you to come first for me.” He looked down at you. 

He hooked his arm under your leg, thrusting faster as he began to rub the sensitive nub. It was at the moment you viced around him, milking his cock while you cried out his name as he pulsed and came in the condom. 

His collapsed against you; his weight was comforting as he worked you through your orgasm, kissing you passionately, then he pulled out gently discarding the condom in a trash bag in the van. 

He rolled to his back as he pulled you to him. 

As you laid on his chest facing him, you beamed; your smile was so wide. “Oh My God Dean. That was amazing. You were amazing. Thank you.”

He laughed. “I guess I should say you’re welcome.”

“Yes.” You giggled like a schoolgirl.

“You were pretty awesome too sweetheart. How do you feel?” He kissed your forehead.

You kissed his chest underneath you. “I wish I had done this a long time ago.”

“You do?” He looked at you curiously. 

You looked up at him. “With you... Of course.” Then you felt weird about the age difference.

He smiled. “You don’t know how long I’ve wanted this with you, but I knew our age difference, it would be tough. Our age difference is just a number. It’s not like you’re old enough to have me as your child. You were just going into first grade.”

“Ugh! Don’t remind me. You weren’t even born then. I’m so sorry Dean.” You felt guilty, like a seductress. 

He looked at you serious. “Don’t. We’re both adults. You were totally worth my time.”

You smiled. “You were too,” referring to the virginity aspect. “I’ll never forget you.”

He laughed. “I hope you won’t forget more than that one reason. Let’s get a little rest and we can go for a second round.”

You smiled back. “OK.”

You slowly fell asleep to the rhythm of his breathing under you.

An hour later you awoke to see Dean naked and asleep on his back next to you. It was a vision that you never wanted to leave your head. His erection was back and you couldn’t help it, but you looked at it amazed at the pleasure he gave you. It was purple and leaking precum and you decided you wanted to taste him. You leaned in and took a long lick up the main vein. Dean’s eyes flew open and he raised himself to his elbows to see you giving him a blowjob.

“Hi.” You smile.

“Hey.”

You licked up the vein again as Dean began to pant. You began to swirl your tongue around the tip, then gently took him into your mouth inch by inch until he reached the back of your throat and you began to suck. 

“Oh Fuck. That’s awesome,” Dean grunted as you continued to take him in. He reached down grabbing your head as he began to thrust into your mouth. 

You had given blowjobs before and knew this was something that could happen. He continued fucking your mouth until he pulsed and emptied in you. You licked up everything you can, keeping every drop as you let him go once he went soft. 

“Fuck Y/N!”

You crawled to his face and kissed him, allowing him to taste himself on your tongue. 

He mocked down your body and began eating you out as you moaned and writhed against his mouth. You were crying out in ecstasy; your thighs squeezed his head gently. He was grunting, his long tongue thrusting in you over and over as his thumb rubbed your clit, when the van flew door opened and standing there were your dad, Bobby, and John Winchester. 

Dean was still grunting, lost in the concentration him giving you pleasure, he did not notice them behind him. You squeezed your thighs tightly until he maneuvered his head from between your legs to speak. “Damn Baby. You’re squeezing me so hard I can’t breathe. Not that I’m complaining.” He winked.

“Dean,” you said frantic as you stared ahead. 

Dean turned his head to see your dad, John, and Bobby. His chin was slathered in your arousal and when he turned around, he gave your dad a full view of your pie Dean had just been eating out. 

“Oh Shit Y/N,” your dad yelled.

“Oh God.” You quickly grab the blanket as you covered yourself and Dean moved away from your soaking core and moved under the blanket with you, making sure both your naked bodies were covered.

“What the fuck are you doing Y/N?” Your dad’s face was marred in anger, disgust, and disappointment.

“They’re fucking Jerry. What does it look like?” Bobby was the voice of reason. 

“It looks like my boy was giving the Y/N what she needs. Good job son.” John laughed. 

Your dad’s face shown disgust. 

You looked at your dad and decided to be honest. “Dad. I’m 24 years old. Dean is 18. We’re both old enough. We’re consenting adults.”

“I know you are, but you could have picked a better guy than one that hunts and picks up women everywhere.”

“That’s my son you are talking about Jerry.”

“And that’s my daughter,” your dad retorted.

“Dad. Dean and I have been tiptoeing around this relationship for years. We finally did something about it and I liked it, and I think he did too.”

“You did?” Dean smiled.

“Of course Dean.” You smiled back and he had the urge to kiss you, but didn’t.

“Me too.” He smiled

“Get out of the van Y/N. We’re leaving.” Your Dad was infuriated and adamant.

“No dad. I’m staying right here.” You clung to Dean’s arm with one hand and the blanket with the other. 

“Yeah. You’re kind of interrupting something,” Dean said sarcastically.

“Why you fucking asshole for fucking my daughter and disrespecting me.” Your father started to get into the van, but Bobby got in the way, pushing your dad back and closed the door. “Jerry, they’re adults and with what they’ve seen and deal with, they deserve someone they can share with, even if that includes fucking.”

“That’s my daughter.” Your dad was still fuming he walked back towards Bobby. 

“You can hit me Jerry. It’s not going to stop those two in there. That boy has been nothing but respectful up until this point. He’s a good kid. They both are. Let them have this.”

Your dad knew you were old enough to make those kind of decisions, but he wasn’t happy about it. He walked off.

Bobby looked at John. “Come on John. Let Romeo finish his job in there.”

“I just hope you have protection son.” John Winchester turned, heading back with Bobby.

“Now where were we?” Dean smiled as he looked at you. 

You felt guilty. You broke your dad’s heart. 

Dean could see the sadness in your face. “Y/N. I don’t want to be the one to ruin sex for you. It’s a beautiful thing and I want to finish this… with you.” He kissed you gently then moved his head back between your legs, licking up your slit, sucking in the nub, and finally moving his fingers back into you. 

Your back arched as you let him continue, moaning his name. You finally came again in a whirlwind feeling of bliss.

Dean moved back up to your face and kissed you. You placed your palms on his cheeks and kissed him tenderly. “Thank you.”

He smiled. “You’re welcome, but we’re not done yet.” He then rolled to his back grabbing another condom from his jeans. “I want you to ride me Baby.”

You crawled over, straddling him, leaned in and   kissed him. You gently rolled the condom on his full length and then aligned his cock to your entrance, moving down, letting him impale you with a blissful sigh. He grabbed your hips as you began undulating on him. Your began building your pace as he reached up and kneaded your breasts. 

“Oh Fuck Dean. This is amazing.”

Dean smiled and grunted. “Fuck! You’re amazing.”

You rode him hard until you finally clenched down around him and he shot his load up into you.. You collapsed on top of him as you peppered him with kisses.

“I love you Dean.” As soon as you said that you froze. “Shit! I mean. I mean.” You didn’t want to scare him off. 

He turned serious as his olive green eyes bore into yours. “I love you Y/N.” He smiles and immediately alleviated your fear that he was just going to sleep with you and leave. 

He kissed you tenderly. You finally rolled over and fell asleep against his chest for the rest of the night. 

The next morning, he held your hand as you walked back to Bobby’s. Your dad’s vehicle was gone as well as John and the Impala. When you entered Bobby’s, you were almost in tears. “Where’s our dads Bobby?” Dean asked.

Bobby looked at you first. “Your dad went on a hunt. He said you were old enough to take care of yourself, but asked if you could stay here for awhile he went on cases.” Bobby turned to Dean. “John said he will be back in a few days. He went on a different hunt. Sam is still asleep in his room.”

Dean looked at you and started to smile, but then saw your sadness. 

“I let my dad down Dean.”

He hugged you. “You didn’t let him down. He had to know his little girl would grow up eventually.”

“I know Dean. It still makes me sad. He was my only family.” 

“No he’s not. You got me, my brother, dad, and Bobby. We are family, Y/N.” He bent down, picking you in his arms and carried you down to your bedroom where he laid you on your bed, gently removed your shoes, and crawled in behind you, spooning you. It was a pure loving and caring gesture.


	3. Chapter 3

You and the Winchesters stayed with Bobby that summer with you and Dean pretty much holed up in that van. He taught you everything you needed to know about sex, which was a lot. You taught him about romance, cuddling, and the sweeter side of love. You were already on the pill for reasons outside of pregnancy, but after you and Dean started sleeping together, it was helpful. 

When your dad arrived back in town in August, he was not happy you were still with Dean, so to keep you from each other, you went back on the road hunting with him, not seeing Dean and the rest of the Winchesters as often as you would like. When you did run into them in town, your dad would try to leave; however, Dean would beat him to it by “borrowings” a local vehicle and you guys would go somewhere remote to be naked and tangled up in each other for a few days to make up for lost time. Then your dad would drag you away and you would both would be back on the road in separate cars to different hunts. 

You met some men along the way, teaching them some of the things Dean taught you which got you some praise, but you always considered that elder Winchester the love of your life. 

Your dad was killed by a demon protecting you when you were 32, the same year John sacrificed himself to Azazel to save Dean’s life after the crash that almost killed him. You sought out Dean after that and met him at Bobby’s where you tried to comfort him, but he was beyond comforting. He was drinking all the time, angry all the time, and sex was almost hate sex, rough and missing the connections you once had, so you kissed him one last time, saying goodbye and left.


	4. Chapter 4

It seemed like every two years or so, you’d start to think of him again and the next thing you knew he would pop back into your life, meeting you on a hunt. Sometimes when you started thinking of him, you couldn’t even go on the internet without looking up hunts you’d think you could see him at, racing to that location to see if you could get there in time to see him. Sometimes you got lucky and he was there, and you would spend a few extra days with him in your hotel room. The days of sex in the back seat of a stolen car were gone; instead, sex in clean sheets in a moderately priced hotel room was enjoyable. You had some money since your dad had money from investments and from the job that he had before your mom had died. 

It was twenty years later and the seventh time you got back with him, when Dean, in a hotel somewhere in Minnesota with you, offered to change your life.

“Come back to the men of letters bunker with me? There’s plenty of room. You can have your own room or share a room with me, or we can just move between rooms.” Dean smiled; your bodies were coming down from the last few hours of amazing sex. 

“Really?” You smiled loving the fact that he wanted you to be with him. 

“Fuck yeah.”

You thought about it as he traipsed his fingers across your abdomen, his lips puckering over a sensitive nipple causing your arousal to pool again. He still turned you on like no other man ever could. 

“OK Dean. Sure.” You smiled and he smirked picking you up and carrying you to the shower where he bent down on his knees, throwing your legs over his shoulders and sucked on your clit, pumping two fingers into you. You came hard writing on his mouth, then he moved up holding your buttocks as you wrapped your arms around his waist and he began thrusting into you. “I love you Y/N.”

“I love you too Dean.”

Two years later and you were a permanent fixture at the bunker researching and being the sister Sam felt he always had, while having a loving, badass boyfriend in Dean, who loved you and protected you . Your life was complete. When it came to the love of your life, I guess it’s never really over. 

**Author's Note:**

> Thank you for reading. Please let me know if you like it.
> 
> Please do not post or disseminate this work on any other site without express written consent of the author.


End file.
